CN108398482A - 2- phenyl -3-（P- aminophenyl）Application of the acrylonitrile as matrix in MALDI-MS analyzes carbohydrate - Google Patents
2- phenyl -3-（P- aminophenyl）Application of the acrylonitrile as matrix in MALDI-MS analyzes carbohydrate Download PDFInfo
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- CN108398482A CN108398482A CN201810212509.0A CN201810212509A CN108398482A CN 108398482 A CN108398482 A CN 108398482A CN 201810212509 A CN201810212509 A CN 201810212509A CN 108398482 A CN108398482 A CN 108398482A
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- maldi
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- acrylonitrile
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/62—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode
- G01N27/626—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode using heat to ionise a gas
- G01N27/628—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode using heat to ionise a gas and a beam of energy, e.g. laser enhanced ionisation
Abstract
Application the present invention relates to 2 phenyl, 3 (p-aminophenyl) acrylonitrile as matrix in MALDI MS analysis carbohydrates, 2 phenyl 3 (p-aminophenyl) acrylonitrile have as reactive matrix for MALDI MS analysis carbohydrates highly sensitive and highly selective, solve that carbohydrate is low in the ionized efficiency of MALDI, the problem of often inhibition by other samples.2 phenyl 3 (p-aminophenyl) acrylonitrile can occur non-reductive amination with the aldehyde radical of carbohydrate and react, therefore carbohydrate derivatization reagent can be used as, to improve Ionization Efficiency of the carbohydrate in MALDI MS, on the other hand, it is also used as MALDI Matrix-assisted saccharide compound desorption ionizations.
Description
Technical field
The present invention relates to field of biochemistry detection, and in particular to 2- phenyl -3- (p- aminophenyl) acrylonitrile (2-
Phenyl-3- (p-aminophenyl) acrylonitrile, PAPAN) fly substance assistant laser desorpted ionized as matrix
Row time mass spectrum (Matrix Assisted Laser Desorption Ionization Mass Spectrometry,
MALDI-MS the application in carbohydrate) is analyzed.
Background technology
MALDI-MS technologies are as a kind of surface laser resolves mass spectrum, and since Tanaka in 1988 et al. is reported, development is fast
The features such as speed has high sensitivity, high-throughput, high-salt tolerance, sample preparation is simple, therefore in biological sample analysis, environment
Analysis, clinic etc. play important role.In MALDI-MS technologies, matrix forms cocrystallization, base with sample to be tested
Matter absorbs laser energy and passes to analyte to assist determinand parsing ionization.Common MALDI matrix is some tools
The organic molecule for having conjugated structure, such as alpha-cyano -4- hydroxycinnamic acids (CHCA), sinapic acid (SA), 3- hydroxy-picolinic acids
(HPA), 2,5-dihydroxybenzoic acid (DHB) etc..In sample analysis, the selection of MALDI matrix plays a crucial role, as CHCA is normal
For analyze polypeptide and albumen less than 10000Da, SA are chiefly used in foranalysis of nucleic acids for albumen, the HPA more than 10000Da and
DHB is suitable for the analysis of polypeptide and polysaccharide.Although there are many related base Quality Research at present, the selection of matrix still with
Based on experience, especially some hardly possiblies are ionized, there are still prodigious challenges for the low sample of abundance such as carbohydrate.
The glycosylation of protein plays in the bioprocess such as protein stability, immunogenicity, intracellular biological conduction
Important role, identification oligosaccharide are particularly significant in glycosylation is studied.The quick analysis of MALDI-MS technologies, it is relatively simple
Spectrum elucidation (MALDI generates single charge peak) is especially suitable for carbohydrate analysis.However, due to the low Ionization Efficiency of carbohydrate,
MALDI-MS analyzes carbohydrate, and there are still prodigious challenges.In addition by other substances with the affine energy of high proton as caused by polypeptide
Depression effect causes carbohydrate analysis difficult, therefore it is extremely urgent that selectivity, which improves the Ionization Efficiency of sugar,.
It is currently used derivatization method to methylate with reduction amination.However, methylating can make different carbohydrates different
Mass-to-charge ratio (m/z) migration, this causes spectrum elucidation difficult, and the sugar to methylate is needed before Mass Spectrometer Method and reaction system
Separation.In recent years, reduction amination reagent such as 2- aminobenzamides (2-AB), 2-aminopyridine (2-AP) is reported in succession can be with
Sugared Ionization Efficiency is improved, but reductive amination process need to use reducing agent NaBCN3, therefore generally requires to remove before detection.
Invention content
The present invention provides applications of the PAPAN as matrix in MALDI-MS analyzes carbohydrate, and PAPAN passes through non-reductive amination
Derivatization carbohydrate is reacted, to improve the Ionization Efficiency of carbohydrate, especially PAPAN has strong absorption at 355nm, can be used as matrix
Assisted carbohydrate ionizes, therefore reacts excessive derivatization reagent and be not required to be separated, and MALDI-MS applies PAPAN when analyzing carbohydrate
The sensitivity that carbohydrate detection is not only increased as matrix also improves the selectivity of carbohydrate detection, solves carbohydrate in MALDI
Ionized efficiency is low, the problem of often inhibition by other samples.Shown in the structural formula of PAPAN of the present invention such as formula (1)：
Applications of the PAPAN of the present invention as matrix in MALDI-MS analyzes carbohydrate, is as follows：
A. by PAPAN and sugared mixed dissolution to be measured in the methanol solution containing 5% acetic acid, reaction 1h is mixed at 65 DEG C
Close solution；
B. it takes the mixed solution point in step a on the mating anchorchip target plates of MALDI mass spectrums, takes pure water point anti-
It answers on liquid, natural drying forms homogeneous sample layer, and the sample after drying is carried out MALD-MS mass spectral analyses.
As more preferably technical solution of the invention：A concentration of 2~5mg/mL of PAPAN described in step a.
As more preferably technical solution of the invention：The volume of mixed solution described in step b is 0.5-1 μ L.
As more preferably technical solution of the invention：Pure water described in step b is 0.5-1 μ L.
The PAPAN synthetic methods are as follows：A. be added first in round-bottomed flask 20mL methanol and 0.115g,
0.005mol metallic sodiums are mixed and become sodium methoxide until metallic sodium is completely dissolved.Then 1.17g, 0.01mol benzene is added
2h is stirred at room temperature until raw material has reacted generation yellow in mixed liquor by acetonitrile and 1.51g, 0.01mol paranitrobenzaldehyde
Precipitation, filtered solid methanol and washing obtain 2.25g glassy yellow products three times；B. step a is added in round-bottomed flask
In 2.5g, 0.01mol glassy yellow product obtained, 40mL ethyl alcohol and 11.3g, 0.05mol stannous chloride dihydrate SnCl2·
2H2O flows back mixture 0.5h.With saturation NaHCO3It is neutralized to alkalescent, is diluted with 50 mL water, is then extracted with chloroform.Extraction
The organic phase taken is dried with anhydrous sodium sulfate, filtering, is used in combination Rotary Evaporators evaporation solvent to obtain 2.09g yellow solids, as
PAPAN。
Compared with prior art, the present invention has the advantages that：
PAPAN has conjugated structure, and synthesis is simply and of low cost, has strong absorption at instrument wavelength 355nm, can be with
Non-reductive amination occurs with the aldehyde radical of carbohydrate to react, PAPAN improves sugar as carbohydrate derivative reagent in MALDI-MS detections
Class degree of ionization, reaction step is simple, does not need other reagents, and the PAPAN for reacting surplus may act as well
The parsing ionization of MALDI Matrix-assisted saccharide compounds, improves sensitivity and selectivity of the MALDI-MS for carbohydrate analysis；
The present invention overcomes carbohydrates often to be inhibited the phenomenon that by other compounds, obtains highly uniform crystallization, improves the reproduction of analysis
Property.
Description of the drawings
Fig. 1 is synthesis PAPAN flow diagrams；
Fig. 2 is the MALDI mass spectrograms of PAPAN；
Fig. 3 is PAPAN uv absorption spectras；
Fig. 4 is the MALDI mass spectrograms for detecting maltose；Fig. 4 a be PAPAN be used as matrix, Fig. 4 b be DHB as base
Matter；
Fig. 5 is aspect graph under the MALDI-MS autogamy microscopes obtained with different spotting methods；
Fig. 6 is detection maltose and polypeptide (1:1) the MALDI mass spectrograms of mixture；Fig. 6 a PAPAN are examined as matrix
It surveys, Fig. 6 b DHB are as matrix；
Fig. 7 is detection maltose and polypeptide (1：10) the MALDI mass spectrograms of mixture；Fig. 7 a PAPAN are examined as matrix
It surveys, Fig. 7 b DHB are as matrix；
Fig. 8 is the MALDI mass spectrograms for detecting ovalbumin enzymolysis product；Fig. 8 a PAPAN are detected as matrix, Fig. 8 b
DHB is as matrix.
Specific implementation mode
The following examples will be further described the present invention, but the present invention is not limited to the following embodiments.
Container as used in the following examples, reagent etc., unless otherwise specified, commercially obtain.Lead to below
Crossing specific embodiment, the present invention will be described, but the present invention is not limited thereto.
The model Autoflex of Matrix assisted laser desorption ionization time of-flight mass spectrometer used in following embodiments
Speed TOF/TOF (Bruker Daltonics, Germany), laser are the Nd of 355nm wavelength:YAG laser.Mass spectrum is surveyed
Try parameter：Accelerating potential：20.000kv；Postpone extraction voltage：18.000kv；The time is drawn in delay：150ns；Reflector voltage：
20.000kv；Lens voltage：6.000kv；Frequency：500Hz.
Embodiment 1：Synthesis PAPAN is simultaneously analyzed, and PAPAN synthesizes schematic diagram as shown in Figure 1, being as follows：
1. 20mL methanol and 0.115g, 0.005mol metallic sodium are added first in round-bottomed flask, it is mixed until gold
Category sodium, which is completely dissolved, becomes sodium methoxide.Then 1.17g, 0.01mol benzene acetonitrile and 1.51g, 0.01mol p-nitrophenyl first is added
2h is stirred at room temperature until raw material has reacted generation yellow mercury oxide, filtered solid methanol and washing in mixed liquor by aldehyde
2.25g glassy yellow products are obtained three times.
2. 2.5g, 0.01mol glassy yellow product obtained in step 1,40mL ethyl alcohol and 11.3 are added in round-bottomed flask
G, 0.05mol stannous chloride dihydrates SnCl2·2H2O flows back mixture 0.5h.With saturation NaHCO3It is neutralized to alkalescent, is used
50mL water dilutes, and is then extracted with chloroform.The organic phase of extraction is dried with anhydrous sodium sulfate, and filtering is used in combination Rotary Evaporators to steam
Hair solvent obtains 2.09g yellow solids, as PAPAN.
PAPAN produced above is subjected to MALDI mass spectrums and ultraviolet absorption spectroscopy, it can be seen that PAPAN exists
It is easy to ionize in MALDI and has strong absorption at 355nm, so PAPAN meets the condition as matrix.
Embodiment 2：PAPAN detects maltose as reactive matrix for MALDI-MS.
1. the maltose mother liquor (aqueous solution) of 10mM is configured, it can 4 DEG C of refrigerators preservations.
2. configuring PAPAN solution in 2.5g/L embodiments 1, solvent for use is the methanol solution containing 5% acetic acid.It can 4 DEG C of ice
Case is kept in dark place.
3. taking PAPAN solution in 99 μ L steps 2 that it is female that maltose in 1 μ L steps 1 is then added in 1.5mL centrifuge tubes
Liquid is uniformly mixed, and is placed in 65 DEG C of water-baths and is reacted 1h.
4. take in 0.5 μ L steps 3 reaction solution point on anchorchip target plates, after take 0.5 μ L pure water points reacting immediately
On liquid, natural drying at room temperature.
5. as a comparison, maltose mother solution gradient is diluted to 10 in step 1-4M takes 1 μ L maltose solution and 1 μ L
(DHB, 10g/L, solvent for use are acetonitrile water mixed liquid, V to common matrix 2,5-dihydroxybenzoic acidAcetonitrile:VWater=1:1) it mixes,
Then take 1 μ L mixed liquor points on anchorchip target plates, natural drying at room temperature.
6. being sent into MALDI-MS to be analyzed.Mass spectrometric data acquires under cation reflective-mode.
PAPAN and DHB is as shown in Figure 4 as substrate assay maltose MALDI mass spectrograms in embodiment 2, it can be seen that
PAPAN detects maltose as matrix, and stronger signal is obtained than common matrix DHB
The crystal habit that two kinds of point sample modes are formed when embodiment 3.PAPAN is as matrix compares.
1. take in 0.5 μ L embodiments 2 reaction solution point on anchorchip target plates, after take 0.5 μ L pure water points anti-immediately
It answers on liquid, the point before reaction solution drying, natural drying at room temperature.
2. taking in 0.5 μ L embodiments 2, reaction solution point is on anchorchip target plates, direct natural drying at room temperature.
3. target plate is sent into MALDI-MS, its pattern is observed.
Fig. 5 left hand views are form under the MALDI-MS autogamy microscopes that the method point sample in embodiment 3 using step 1 obtains
Figure, the right sides Fig. 4 are the aspect graph that the method point sample of 3 step 2 of embodiment obtains, it can be seen that the point sample mode ratio that the present invention uses
General point sample loading mode forms crystallization evenly, is conducive to the reproducibility for improving analysis.
Embodiment 4：PAPAN is as reactive matrix for MALDI-MS detection maltose and mixtures of polypeptides.
1. it is 1 to configure molar ratio:1/1:10 maltose and polypeptide mixing mother liquor, the maltose a concentration of 10
MM, polypeptide sequence Ac-EAIYAAPFAKKK.
2. taking in 1 μ L steps 1, in 99 μ L PAPAN solution, (a concentration of 2.5g/L, solvent are containing 5% acetic acid to mixed solution
Methanol) in, 1h is reacted at 65 DEG C.
3. take in 0.5 μ L steps 2 reaction solution point on anchorchip target plates, after take 0.5 μ L pure water points reacting immediately
On liquid, spontaneously dry at room temperature.
4. as a comparison, maltose and polypeptide mother liquor dilute 100 times in step 1, take the 1 diluted solution of μ L and 1 μ L normal
With matrix 2,5-dihydroxybenzoic acid, (DHB, 10g/L, solvent for use are acetonitrile water mixed liquid, VAcetonitrile:VWater=1:1) it mixes, then
It takes 1 μ L mixed liquor points on anchorchip target plates, spontaneously dries at room temperature.
5. being sent into MALDI-MS to be analyzed.Mass spectrometric data acquires under cation reflective-mode.
Fig. 6 is that detection molar ratio is 1：1 maltose and mixtures of polypeptides obtains MALDI mass spectrograms；Fig. 6 a PAPAN
It is detected as matrix, Fig. 6 b are to use DHB as matrix.
Fig. 7 is that detection molar ratio is 1：10 maltose and mixtures of polypeptides obtains MALDI mass spectrograms；Fig. 5 a are to use
PAPAN is detected as matrix, and Fig. 5 b are to be detected with DHB.
M represents maltose in Fig. 6 and Fig. 7, and * represents polypeptide and adds hydrogen or add alkali metal ion.By detecting oligosaccharide
With polypeptide bulk testing, it can be seen that use PAPAN as reactive matrix, have good selectivity to carbohydrate, overcome carbohydrate
By polypeptide etc. there is the substance of the affine energy of high proton to inhibit the phenomenon that.
Embodiment 5:N-s of the PAPAN as derivatization reagent and matrix for MALDI-MS detection ovalbumin enzymolysis releases
Sugar.
1. ovalbumin and trypsase (30:1, W:W it is water-soluble that 200uL 50mM NH4HCO3 (PH=7.8)) are dissolved in
In liquid (a concentration of 0.5mg/mL of ovalbumin), incubation 12h is digested at 37 DEG C.And then 1 μ L peptide-N- glucosides is added
Enzyme (PNGase F) is incubated 18h progress oligosaccharide releases at 37 DEG C.
2. take the ovalbumin enzymolysis product obtained in 100 μ L steps 1 to be freeze-dried its solvent that volatilizees, it can -20 DEG C of refrigerators
It preserves.
3. be added in the ovalbumin enzymolysis product obtained in step 2 100 μ L PAPAN solution (a concentration of 2.5 g/L,
Solvent is the methanol containing 5% acetic acid) in, 1h is reacted at 65 DEG C.
4. take in 0.5 μ L steps 3 reaction solution point on anchorchip target plates, after take 0.5 μ L pure water points reacting immediately
On liquid, spontaneously dry at room temperature.
5. the ovalbumin enzyme digestion reaction liquid obtained in 1 μ L steps as a comparison, is taken often to use matrix 2,5- dihydroxies with 1 μ L
(DHB, 10g/L, solvent for use are acetonitrile water mixed liquid, V acetonitriles to yl benzoic acid:Water=1 V:1) it mixes, then takes 1uL mixed liquors
Point spontaneously dries on anchorchip target plates.
6. being sent into MALDI-MS to be analyzed.Mass spectrometric data acquires under cation linear model.
Fig. 8 is the MALDI mass spectrograms for detecting ovalbumin enzymolysis product；Fig. 8 a are to use PAPAN as matrix；Fig. 8 b are
Use DHB as matrix.Number 1-21 represents ovalbumin N- sugar in figure and PAPAN reaction products add the peak of Na.The N- detected
Sugared structural information is as shown in table 1.
It can be seen that PAPAN can the choosing from ovalbumin enzymolysis product (trypsin+PNGase F) from embodiment 5
Selecting property detects oligosaccharide, and DHB only detects peptide fragment.The present embodiment has further demonstrated that PAPAN has height to carbohydrate detection
Selectivity.
Table 1：N- glycan molecules amount, structural information in ovalbumin.
Claims (5)
- Application of 1.2- phenyl -3- (p- aminophenyl) acrylonitrile as matrix in MALDI-MS analyzes carbohydrate.
- 2. 2- phenyl -3- (p- aminophenyl) acrylonitrile as described in claim 1 analyzes carbohydrate as matrix in MALDI-MS In application, be as follows：A. by PAPAN and sugared mixed dissolution to be measured in the methanol solution containing 5% acetic acid, reaction 1h obtains mixing molten at 65 DEG C Liquid；B. it takes the mixed solution point in step a on the mating anchorchip target plates of MALDI mass spectrums, takes pure water point in reaction solution On, natural drying forms homogeneous sample layer, and the sample after drying is carried out MALD-MS mass spectral analyses.
- 3. 2- phenyl -3- (p- aminophenyl) acrylonitrile as described in claim 1 analyzes carbohydrate as matrix in MALDI-MS In application, a concentration of 2~5mg/mL of the PAPAN described in step a.
- 4. 2- phenyl -3- (p- aminophenyl) acrylonitrile as described in claim 1 analyzes carbohydrate as matrix in MALDI-MS In application, the volume of the mixed solution described in step b is 0.5-1 μ L.
- 5. 2- phenyl -3- (p- aminophenyl) acrylonitrile as described in claim 1 analyzes carbohydrate as matrix in MALDI-MS In application, pure water described in step b is 0.5-1 μ L.
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| CN114460162A (en) * | 2022-01-11 | 2022-05-10 | 生物岛实验室 | MALDI (matrix-assisted laser Desorption) detection method of small molecular oligosaccharide |
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